My firm just announced they are going to be laying off 1,500 employees. I don’t know if I am going to be one of them, but I would not be averse to receiving “a package” if it was good enough. Is there a risk in telling my boss that I might be interested in being laid off?

The only risk is to your ego if he lights up like a Christmas tree and then has to feign surprise and disappointment. But, seriously, there is a real risk is if you don’t make the proper approach and your boss had no intention of letting you go. So pick a quiet moment and just explain that you’d rather control your own destiny and help the company, so if your job is potentially at risk you’d be open to discussing something now to make for a smooth transition for all. Alternatively, you could simply say that you are exploring your options and even if you aren’t on the target list you’d be open to discussing what the package would be. If you choose to go that route, it might save someone else’s job.

When handled in that professional manner, the worst that’s likely to happen is your boss says you’re too valuable and he isn’t going to make it easy for you to leave.

My employer reprimanded me for a comment I made on Twitter that they deemed disparaging to the company. Can they do that? Isn’t that a violation of my free speech rights?

They aren’t violating your right to free speech. They are exercising their own right to say they don’t like you publicly disparaging the hand that feeds you. Every employee has a duty of loyalty to their company to further the company’s interests and not damage the company. The exceptions are when an employee is exposing unlawful or unethical practices, which every employee has an obligation to do if they are aware of such practices, because exposing them is actually for the greater good. (There are whistle-blower laws protecting employees in such instances) If you just want to chirp negative stuff about your employer publicly, that is your right — but your employer also has the right to “unfollow” you — if you follow . . .